Diphenyl(meth)acrylamide-containing thermosetting resin composition and cured product therefrom

Abstract

A thermosetting resin composition having low dielectric constant, low dielectric loss tangent, high glass transition point, and excellent water resistance, and cured product therefrom. The thermosetting resin composition includes the following components (A) and (B). (A) a compound of formula (I) (X 1 and X 2 each independently represent a C1-C20 alkyl group or the like, n1 and n2 each independently represent 0 or 1, Z 1 and Z 2 each independently represent a single bond or the like, X 3 and X 4 each independently represent an organic group or the like, m1 and m2 each independently represent any integer from 0 to 4, and Y represents a polymerizable functional group) (B) a maleimide compound having one or more maleimide groups, a polyphenylene ether compound, polybutadiene, a styrene-butadiene-styrene block copolymer, or polymer having repeat unit of formula (III) (Z 3 represents C6-C12 arylene group, and R 2 to R 7 each independently represent hydrogen atom or the like).

1 . A thermosetting resin composition comprising:
 (A) at least one compound of formula (I):   
       
         
           
           
               
               
           
         
         (wherein
 X 1  and X 2  each independently represent a C1-C20 alkyl group, a C1-C20 alkoxy group, a C3-C6 cyclic alkyl group, a C3-C6 cyclic alkoxy group, a benzyl group, or an α,α-dimethylbenzyl group, 
 n1 and n2 each independently represent 0 or 1, 
 Z 1  and Z 2  each independently represent a single bond or a C1-C3 alkylene group, 
 X 3  and X 4  each independently represent an organic group or a halogeno group, 
 m1 and m2 each independently represent any integer from 0 to 4, and 
 Y represents a polymerizable functional group), and 
 
         (B) at least one of the following (B-1) to (B-5):
 (B-1) a maleimide compound having one or more maleimide groups; 
 (B-2) a polyphenylene ether compound; 
 (B-3) polybutadiene having a molar ratio of 1,2-bond structure to 1,4-bond structure of 80:20 to 100:0; 
 (B-4) a styrene-butadiene-styrene block copolymer (SBS) having a molar ratio of 1,2-bond structure to 1,4-bond structure in the butadiene block of 80:20 to 100:0; and 
 (B-5) a polymer having a repeat unit of formula (III) in the molecule: 
 
       
       
         
           
           
               
               
           
         
         
           (wherein Z 3  represents a C6-C12 arylene group, R 2  to R 4  each independently represent a hydrogen atom or a C1-C6 alkyl group, and R 5  to R 7  each independently represent a hydrogen atom or a C1-C6 alkyl group). 
         
       
     
     
         2 . The thermosetting resin composition according to  claim 1 , further comprising (C) a radical polymerization initiator. 
     
     
         3 . The thermosetting resin composition according to  claim 1 , wherein the compound of formula (I) is a compound of formula (II): 
       
         
           
           
               
               
           
         
         (wherein
 X 5  and X 6  each independently represent a C1-C20 alkyl group, a C1-C20 alkoxy group, a C3-C6 cyclic alkyl group, a C3-C6 cyclic alkoxy group, a benzyl group, or an α,α-dimethylbenzyl group, and 
 R 1  represents a hydrogen atom or a methyl group). 
 
       
     
     
         4 . A cured product made by curing the thermosetting resin composition according to  claim 1 . 
     
     
         5 . The thermosetting resin composition according to  claim 1 , wherein the thermosetting resin composition is a resin composition for the insulating layer of a printed wiring board. 
     
     
         6 . A resin varnish comprising the thermosetting resin composition according to  claim 1 . 
     
     
         7 . A prepreg comprising a substrate impregnated with the thermosetting resin composition according to  claim 1 . 
     
     
         8 . An adhesive film having a resin composition layer comprising the thermosetting resin composition according to  claim 1  on a support film. 
     
     
         9 . A metal foil with a thermosetting resin composition, having a resin composition layer comprising the thermosetting resin composition according to  claim 1  on the metal foil. 
     
     
         10 . A laminate with a metal foil, comprising:
 a layer of a cured product of the thermosetting resin composition according to  claim 1 ; and   a metal foil.   
     
     
         11 . The thermosetting resin composition according to  claim 2 , wherein the compound of formula (I) is a compound of formula (II): 
       
         
           
           
               
               
           
         
         (wherein
 X 5  and X 6  each independently represent a C1-C20 alkyl group, a C1-C20 alkoxy group, a C3-C6 cyclic alkyl group, a C3-C6 cyclic alkoxy group, a benzyl group, or an α,α-dimethylbenzyl group, and 
 R 1  represents a hydrogen atom or a methyl group). 
 
       
     
     
         12 . A cured product made by curing the thermosetting resin composition according to  claim 2 . 
     
     
         13 . The thermosetting resin composition according to  claim 2 , wherein the thermosetting resin composition is a resin composition for the insulating layer of a printed wiring board. 
     
     
         14 . A resin varnish comprising the thermosetting resin composition according to  claim 2 . 
     
     
         15 . A prepreg comprising a substrate impregnated with the thermosetting resin composition according to  claim 2 . 
     
     
         16 . An adhesive film having a resin composition layer comprising the thermosetting resin composition according to  claim 2  on a support film. 
     
     
         17 . A metal foil with a thermosetting resin composition, having a resin composition layer comprising the thermosetting resin composition according to  claim 2  on the metal foil. 
     
     
         18 . A laminate with a metal foil, comprising:
 a layer of a cured product of the thermosetting resin composition according to  claim 2 ; and   a metal foil.